65,787

Monroe County, FL Homes

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  • /43

    $1,175,000

    $75K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,368 Sq Ft

    27395 Saint Lucie Ln, Summerland Key, FL 33042

    Welcome to your piece of paradise in Breezeswept Beach Estates, where laid-back island living meets premier canal-frontage. From here, it's an easy cruise to open water--perfect for early morning fishing runs, sunset sails, or spontaneous sandbar days. Inside, this bright and breezy retreat has been thoughtfully updated with stainless steel appliances, sleek Silestone countertops, and warm

    Agent Photo

    Michelle Vanhoose

    Coldwell Banker Schmitt Real Estate Co.

    27395 Saint Lucie Ln, Summerland Key, FL 33042
  • /14

    $5,100 Per Month

    • 2 Beds
    • 2 Baths
    • 1,311 Sq Ft
    • Condo for Rent

    1800 Atlantic Blvd Unit C127, Key West, FL 33040

    Property Id: 2599443 As one of the most coveted condominium properties in Key West, 1800 Atlantic is iconic for its oceanfront location, lush gardens, and spectacular pool setting overlooking the ocean. The heated, salt-water, Olympic-sized pool, jacuzzi hot-tub and lounge seating area is the centerpiece of this beautifully cared-for property. Tennis enthusiasts, will have access to 3 tennis

    1800 Atlantic Blvd Unit C127, Key West, FL 33040
  • /45

    $1,550,000

    Sold Jan 30, 2026

    28538 John Silver Rd, Summerland Key, FL 33042

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft
    • Built 1981

    Last Sold Summary

    • 3% Below List Price
    • $1,242/SF
    • 164 Days On Market

    Current Estimated Value $1,552,288

    Last Listing Agent Diane Corliss Coldwell Banker Schmitt RE Co.

    28538 John Silver Rd, Summerland Key, FL 33042
    • /2

      Est $302,000

      Not Listed For Sale

      104000 Overseas Hwy Unit 1, Key Largo, FL 33037

      • 3 Beds
      • 3 Baths
      • 2,400 Sq Ft
      • Built 2008
      104000 Overseas Hwy Unit 1, Key Largo, FL 33037

  • /16

    $419,000

    $80K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 460 Sq Ft

    6 Beach Dr, Key West, FL 33040

    Rare DOUBLE SIZE LOT on OPEN WATER with BOATING ACCESS and ROGO EXEMPT LETTER IN HAND!! This lot offers magnificent sunset views over the open water and has plenty of room to add a dock for your boat. There is a canal cut around the perimeter of Saddlebunch Key giving the property shallow boating access to the Atlantic and Gulf. This subdivision has a nice park with tennis & pickleball courts,

    Agent Photo

    Anneliese Dietrick

    Coldwell Banker Schmitt RE Co.

    6 Beach Dr, Key West, FL 33040
  • /20

    $5,715

    Total Monthly Price

    • 4 Beds
    • 3 Baths
    • 1,797 Sq Ft
    • Condo for Rent

    1315 Whitehead St Unit SI ID1297834P, Key West, FL 33040

    The advertised rate of $5,715/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 17, 2027.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1315 Whitehead St Unit SI ID1297834P, Key West, FL 33040
  • /56

    $880,000

    Sold Apr 15, 2026

    82260 Overseas Hwy, Islamorada, FL 33036

    • 3 Beds
    • 3 Baths
    • 2,314 Sq Ft
    • Built 1964

    Last Sold Summary

    • 22% Below List Price
    • $380/SF
    • 276 Days On Market

    Current Estimated Value $972,514

    Last Listing Agent The Florida Keys Sold Sisters Ocean Sotheby's International Realty

    82260 Overseas Hwy, Islamorada, FL 33036
    • /62

      Est $6,226,563

      Not Listed For Sale

      216 Tide Ave, Tavernier, FL 33070

      • 4 Beds
      • 4.5 Baths
      • 3,600 Sq Ft
      • Built 1985
      216 Tide Ave, Tavernier, FL 33070

      Last Sold Summary

      • 16 Days On Market

  • /65

    $5,650,000

    $1M PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,649 Sq Ft

    10987 County Road 905, Key Largo, FL 33037

    Discover unparalleled privacy and tranquility in this one-of-a-kind oceanfront estate, a true sanctuary nestled amidst the untouched beauty of the Florida Keys. Tucked behind a private gate, the estate begins with a scenic drive through acres of pristine, preserved nature, leading to your own private island. This secluded haven, like no other in the Florida Keys, was once a source of inspiration

    Agent Photo

    Pierre-Marc Bellion

    Ocean Sotheby's International Realty

    10987 County Road 905, Key Largo, FL 33037
  • /14

    $2,300 Per Month

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    4D 10th Ave Unit B units, Stock Island, FL 33040

    Property Id: 2725581 Location : D4 10th Ave Stock Island This is one bedroom Apt $2300 per month rent all utilities are included . Washer, dryer in the unit and fence up private yard. 10 minutes to Down town Key west . Require security deposit $2300 and first month rent $2300 to move in. Contact # Grace Thanks.

    4D 10th Ave Unit B units, Stock Island, FL 33040
  • /69

    $1,512,500

    Sold Jul 20, 2026

    24 Mutiny Place, Key Largo, FL 33037

    • 4 Beds
    • 3 Baths
    • 2,252 Sq Ft
    • Built 2001

    Last Sold Summary

    • 2% Below List Price
    • $672/SF
    • 26 Days On Market

    Current Estimated Value $1,563,821

    Last Listing Agent Sally Stribling Coldwell Banker Schmitt Key Largo

    24 Mutiny Place, Key Largo, FL 33037
    • /2

      Est $755,458

      Not Listed For Sale

      51 Riviera Dr, Key West, FL 33040

      • 2 Beds
      • 1 Bath
      • 651 Sq Ft
      • Built 2011
      51 Riviera Dr, Key West, FL 33040

  • /27

    $1,055,000

    $110K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,344 Sq Ft

    29051 Magnolia Ln, Big Pine Key, FL 33043

    Experience Florida Keys waterfront living in the heart of Big Pine Key. This canal-front home with a full concrete seawall and direct boating access offers an exceptional opportunity to enjoy the relaxed Lower Florida Keys lifestyle surrounded by world-class fishing, diving, and boating. The elevated main home features a 2 bedroom, 2 bathroom layout with an open living area, spacious kitchen with

    Agent Photo

    Yvette Toledo-Baste

    COMPASS FLORIDA LLC

    29051 Magnolia Ln, Big Pine Key, FL 33043
  • /13

    $2,800

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 792 Sq Ft
    • Condo for Rent

    3312 Northside Dr Unit 111, Key West, FL 33040

    Available NOW through January 30,2027!Welcome to paradise in Santa Clara Condominiums — a beautifully renovated, fully furnished 2 Fully renovated kitchen & bathroomsHurricane-impact windows & doorsSpacious walk-in storage/closet spacePrivate patio & secluded yard areaDirect access to tennis courts & poolOn-site laundry & secure entryJust minutes from beaches,

    3312 Northside Dr Unit 111, Key West, FL 33040
  • /6

    $2,200

    Sold May 15, 2026

    91865 Overseas Hwy Unit 106, Tavernier, FL 33070

    • 1 Bed
    • 1 Bath

    Last Sold Summary

    • 8% Below List Price
    • 6 Days On Market

    Last Listing Agent Kevin Cornell Cornell Commercial Real Estate, Inc.

    91865 Overseas Hwy Unit 106, Tavernier, FL 33070
    • /63

      Est $1,964,276

      Not Listed For Sale

      17057 Bonita Ln W, Sugarloaf Key, FL 33042

      • 3 Beds
      • 3 Baths
      • 2,366 Sq Ft
      • Built 2015
      17057 Bonita Ln W, Sugarloaf Key, FL 33042

      Last Sold Summary

      • 190 Days On Market

  • /27

    $599,000

    • 2 Beds
    • 1.5 Baths
    • 1,324 Sq Ft

    653 Colson Dr, Key Largo, FL 33037

    Wonderful Opportunity in the Heart of Key Largo! This charming concrete home plus storage offers an excellent foundation for creating your own Florida Keys retreat. Ideally located directly across from John Pennekamp Coral Reef State Park, you'll enjoy one of the most desirable and convenient locations in Key Largo, close to shopping, dining, schools, boating, and an easy commute to Miami.

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    653 Colson Dr, Key Largo, FL 33037
  • /34

    $2,950

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 300 Sq Ft
    • Condo for Rent

    818 White St Unit 5, Key West, FL 33040

    Specials: Get 5% off for a month stay or a deep discount for 6-month bookings in 2026! Available May till October 2026Refundable Security Deposit: $1200.00 (Note: First month's rent, security deposit, and last month's rent are due upfront for long-term rentals.)Additional Features: pool access, porches, private entrance Rebuilt in 2005, this unique home offers modern

    818 White St Unit 5, Key West, FL 33040
  • /55

    $5,325,000

    Sold Jun 22, 2026

    75560 Overseas Hwy, Islamorada, FL 33036

    • 4 Beds
    • 4 Baths
    • 3,228 Sq Ft
    • Built 2005

    Last Sold Summary

    • 11% Below List Price
    • $1,650/SF
    • 168 Days On Market

    Current Estimated Value $6,043,210

    Last Listing Agent Krissy Carnahan Paradise Florida Keys Real Estate, a Luxury Brand

    75560 Overseas Hwy, Islamorada, FL 33036
    • /6

      Est $2,108,729

      Not Listed For Sale

      241 Pueblo St, Tavernier, FL 33070

      • 3 Beds
      • 3 Baths
      • 2,154 Sq Ft
      • Built 2017
      241 Pueblo St, Tavernier, FL 33070

      Last Sold Summary

      • 52 Days On Market

  • /55

    $1,275,000

    Under Contract
    • 2 Beds
    • 1 Bath
    • 960 Sq Ft

    1 Snipe Rd, Key Largo, FL 33037

    Coastal Cottage w/ 65ft of waterfront on an 80ft wide canal - just 1 street in from the Bay in Key Largo! This carefully curated waterfront stilt home has been thoughtfully designed & completely renovated from top to bottom, incl. a new metal roof, impact windows & doors, HVAC, electrical, plumbing, tankless water heater, flooring, kitchen & bath, landscaping, fencing, concrete coatings & more.

    Agent Photo

    Lorie Leal

    American Caribbean Real Estate, Christie's International Real Estate

    1 Snipe Rd, Key Largo, FL 33037
  • /14

    $2,675

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 368 Sq Ft
    • Condo for Rent

    1318 Duncan St Unit 3, Key West, FL 33040

    AVAILABLE JULY. Lease at $2675 per month for a yearly lease. Renovated detached pool view cottage with stainless range and fridge/freezer close to vibrant White St with its cafes and restaurants, gourmet food stores, galleries and yoga studios. A short walk or bike ride to the beaches and the heart of Old Town, the Historic Seaport and Duval Street.....The compound has a large pool shared with

    1318 Duncan St Unit 3, Key West, FL 33040
  • /26

    $295,000

    Sold Jan 08, 2026

    6099 Overseas Hwy Unit 13E, Marathon, FL 33050

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft
    • Built 1976

    Last Sold Summary

    • 15% Below List Price
    • $454/SF
    • 90 Days On Market

    Last Listing Agent Casey Elliott Key Colony Beach Realty

    6099 Overseas Hwy Unit 13E, Marathon, FL 33050
    • /40

      Est $1,028,801

      Not Listed For Sale

      13 Garden Cove Dr, Key Largo, FL 33037

      • 5 Beds
      • 3 Baths
      • 2,400 Sq Ft
      • Built 2024
      13 Garden Cove Dr, Key Largo, FL 33037

      Last Sold Summary

      • 240 Days On Market

  • /54

    $988,999

    $210K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,598 Sq Ft

    9812 Windward Ave, Key Largo, FL 33037

    Live like you're on vacation! Welcome to the resort style living you've been dreaming of--complete with Deeded Boat Slip #3 and an 8,000 lb boat lift just steps from the community boat ramp. This spacious 3-bedroom, 2-bath townhome also features an enclosed lower-level recreation area approximately 1000 sf., with a full bath, ideal for guests, hobbies, or flexible living. Inside, you'll find

    Agent Photo

    Terry Canto

    American Caribbean Real Estate, Christie's International Real Estate

    9812 Windward Ave, Key Largo, FL 33037
  • /8

    $2,900

    Total Monthly Price

    • 1 Bed
    • 1 Bath
    • 1,200 Sq Ft
    • Condo for Rent

    8 Hilton Haven Rd, Key West, FL 33040

    This 1-bedroom, (with additional bonus room for office, workout equipment, art studio etc) 1 large bathroom with double sinks . canal property on Hilton Haven Rd offers 1,200 square feet of living space. The living room provides ample room for relaxation and features ceiling fans for comfort. The kitchen is equipped with a refrigerator, freezer, microwave, dishwasher, and includes a washer

    8 Hilton Haven Rd, Key West, FL 33040
  • /25

    $600,000

    Sold Feb 20, 2026

    10 Verde Dr, Key West, FL 33040

    • 1 Bed
    • 1 Bath
    • 525 Sq Ft
    • Built 2013

    Last Sold Summary

    • 4% Below List Price
    • $1,143/SF
    • 56 Days On Market

    Current Estimated Value $599,417

    Last Listing Agent Sean Farrer Coldwell Banker Schmitt RE Co

    10 Verde Dr, Key West, FL 33040
    • /3

      Not Listed For Sale

      33 Judy Place, Key Largo, FL 33037

      • 3 Beds
      • 2 Baths
      • 1,152 Sq Ft
      • Built 1973
      33 Judy Place, Key Largo, FL 33037

      Last Sold Summary

      • 18 Days On Market

  • /43

    $2,695,000

    $130K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,902 Sq Ft

    525 Louisa St, Key West, FL 33040

    A fantastic renovation of a classic Old Town Key West property, blending timeless charm with modern upgrades. First Impressions are made with a wonderful front porch greeting you as you step from your two off street parking spots--or arrive by bicycle & use the separate entrance with dedicated bike storage.Outdoor Living -A complete irrigation system with landscape lighting transforms the

    Agent Photo

    J. Michael Caron

    Keller Williams Key West Compass Realty

    525 Louisa St, Key West, FL 33040
  • /13

    $2,700

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • House for Rent

    108 Caribbean Ave, Tavernier, FL 33070

    Ready to Move!!Beautifully maintained and freshly painted back-unit duplex (2 bed / 1 bath), centrally located in Tavernier, within walking distance to Harry Harris Beach and Park.This unit features modern bathroom, an updated kitchen, along with central A/C and laundry room with washer and dryer. Enjoy the convenience of parking for up to four vehicles, space for a boat and a

    108 Caribbean Ave, Tavernier, FL 33070
  • /12

    $1,050,000

    Sold Mar 03, 2026

    619 Front St Unit 21, Key West, FL 33040

    • Built 1985

    Last Sold Summary

    • 5% Below List Price
    • 86 Days On Market

    Last Listing Agent Dawn Gonet Berkshire Hathaway HomeServices Knight & Gardner Realty

    619 Front St Unit 21, Key West, FL 33040
    • /46

      Not Listed For Sale

      2 Oakwood Ave, Key Largo, FL 33037

      • 3 Beds
      • 2 Baths
      • 1,484 Sq Ft
      • Built 1991
      2 Oakwood Ave, Key Largo, FL 33037

      Last Sold Summary

      • 62 Days On Market

  • /19

    $1,299,000

    • 7 Beds
    • 4 Baths
    • 2,699 Sq Ft

    1614 Dennis St, Key West, FL 33040

    Investment Opportunity - Income-Producing Triplex!Don't miss this excellent income-producing triplex located in a convenient, high-demand area close to schools, shopping, dining, parks, and just minutes from downtown Key West. Whether you're looking to expand your investment portfolio or occupy one unit while generating rental income from the others, this property offers outstanding

    Agent Photo

    Matthew Sheehan

    Ocean Sotheby's International Realty

    1614 Dennis St, Key West, FL 33040
  • /20

    $5,000

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • House for Rent

    1102 Pearl St, Key West, FL 33040

    Totally restored historic conch furnished pool home. On site parking, one bedroom, den, one interior bath, one pool side bath, IPE deck, central AC, Exposed beam ceilings, loft and pool. Very High quality renovation. Available monthly or annually. Pool heater, central AC, Viking & Wolf appliances, sleeps 6. King bed in bedroom, den has a pull out couch, living room has a pull out couch, you

    1102 Pearl St, Key West, FL 33040
  • /33

    $550,000

    Sold Jun 17, 2026

    57485 Gibson St, Marathon, FL 33050

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft
    • Built 1996

    Last Sold Summary

    • 4% Below List Price
    • $521/SF
    • 77 Days On Market

    Current Estimated Value $570,887

    Last Listing Agent Steven Conley Compass Florida LLC - Tavernier

    57485 Gibson St, Marathon, FL 33050
    • /24

      Est $1,957,386

      Not Listed For Sale

      108 S Bahama Dr, Marathon, FL 33050

      • 4 Beds
      • Built 2023
      108 S Bahama Dr, Marathon, FL 33050

      Last Sold Summary

      • 187 Days On Market

  • /63

    $1,095,000

    $100K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,720 Sq Ft

    2309 Flagler Ave, Key West, FL 33040

    Nestled within a private tropical oasis on a 7,500-square-foot lot, this charming Mid-Century Modern home offers the perfect blend of architectural character and island living. Approximately 64 feet of floor-to-ceiling sliders and windows fill the home with natural light and frame lush garden views from nearly every room.The three-bedroom, two-bath floor plan features clean modern lines,

    Agent Photo

    Jennifer Newman

    Truman & Co. (KW)

    2309 Flagler Ave, Key West, FL 33040
  • /10

    $3,300

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • 960 Sq Ft
    • House for Rent

    563 49th St, Marathon, FL 33050

    Escape to year-round paradise in this charming 2-bedroom, 1-bathroom canal-front half duplex in Marathon, Florida Keys! Offering tranquil waterfront views and a private 24-foot dock, this cozy retreat is perfect for boating enthusiasts, anglers, or anyone seeking a relaxed tropical lifestyle.Property Features:Bedrooms: 2 | Bathrooms: 1 | Sleeps: 6Waterfront Living: Screened-in

    563 49th St, Marathon, FL 33050
  • /51

    $2,498,000

    Sold Jun 17, 2026

    611 Sombrero Beach Rd, Marathon, FL 33050

    • 5 Beds
    • 4 Baths
    • 2,656 Sq Ft
    • Built 2023

    Last Sold Summary

    • $941/SF
    • 28 Days On Market

    Current Estimated Value $2,460,171

    Last Listing Agent Ginger Henderson Coldwell Banker Schmitt Real Estate Co.

    611 Sombrero Beach Rd, Marathon, FL 33050
    • /30

      Not Listed For Sale

      81 Tarpon Basin Dr, Key Largo, FL 33037

      • 2 Beds
      • 1 Bath
      • 470 Sq Ft
      • Built 1965
      81 Tarpon Basin Dr, Key Largo, FL 33037

      Last Sold Summary

      • 8 Days On Market

Showing Results 161 - 200, Page 5 of 18

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